Vacation rentals with a pool in Westhampton

Mamma Mia Getaway

Escape this holiday season to Eastport, NY, and indulge in a memorable stay at this spacious 4-bedroom, 2-bathroom vacation rental house. With a dreamy yard, and a deck, this home has everything needed for a relaxing getaway. Explore nearby attractions such as the captivating wineries and breweries, apple picking, the vibrant Montauk Point Lighthouse, and the unspoiled beauty of the Hamptons. After a day of adventure, return home to unwind by the deck or in the cozy bar room. Eastport awaits!

1940’s Westhampton renovated bungalow

Come stay at this centrally located hamptons chic property. The whole group will enjoy easy access to many beaches, downtown Westhampton Beach and many NoFo wineries. Westhampton Beach is 6 minutes from the house and filled with many amazing restaurants and shops to explore. Explore all of the Hamptons and Northfork from this beautiful 4 bed and 3.5 bath home with inground pool. Pool open MDW- LDW *** No smoking or drugs on property. ***No pets Please note there is no fence around the pool.

Hamptons Oasis | Saltwater Pool, Hot Tub & Games

Welcome to our renovated 3-bedroom retreat in the pristine East Quogue community! You're just a 10-minute drive from both ocean and bay beaches. Revel in the great outdoors with a saltwater pool, hot tub, fire pit, bocce court, and ping pong — plus a backyard grill and spacious patio and deck for seating and dining. Whether you are planning an elevated weekend getaway with friends and family, or need a change in scenery for your work-from-home lifestyle, this is the perfect home to do both.

Luxurious Hamptons Beach Heated Pool Wineries

U.S. Open. Home completely renovated. Chefs kitchen fully stocked with all that you need. CAC throughout our home. A 20x40 inground swimming pool, open from Memorial Day to Labor Day. The pool is normally 80° sometimes can be warmer depending upon the sun. Heating is available for an additional fee. Minutes from the Beach with daily parking available for a fee. Our home is centrally located to the beaches, shops, wineries and golfing yet far enough away that you can enjoy and relax.

Joyful Beach House, viewing The Great South Bay

Amazing Great South Bay view with access to Shorefront and Rider Parks. This Ranch has an unobstructed view of the Shorefront Band Shell. Watch concerts and sunsets from the comfort of your patio. Walk down to the Patchogue Beach Club and enjoy the pool and beach. This open-concept home has 2 bedrooms, one bath, a remodeled bathroom, and a kitchen. The kitchen has stainless steel appliances, a farm sink, and a butcher block countertop with natural lighting that will brighten the home.

Charming & Bright Pool Cottage

Take a deep breath when you enter this very bright, well appointed pool cottage. Lush backyard with the main residence and use of the salt water, unheated pool and outdoor shower. Property is on a tree lined street that ends at the bay. A 5 minute walk to the quaint village of East Quogue. Want to hit the fabulous Hampton beaches, they are a 10 minute drive away. Closest downtown Hamptons are Hampton Bays (5 min), Westhampton (our favorite ...10 min) and Southampton (15 min).

Chic Hamptons Gateway | Pool, Hot Tub, Beach

Stylish & airy Hamptons retreat on over an acre, 5 min to ocean beaches and Westhampton Village. Thoughtfully designed, this home features 4 bedrooms, 3 full baths, and a modern open layout across 2 floors. Outside, a heated pool, hot tub and fully fenced yard offer space to unwind in privacy. Clean design, abundant natural light, seamless indoor-outdoor flow, and a calm vibe make this home ideal for an escape. Enjoy peaceful mornings, beach walks, and cozy nights by the fireplace.

Brand new house with an all year round hot tub.

Your family will be close to everything when you stay at this centrally-located place. Very close beaches near dune road. Movie theaters, supermarkets, liquor store, farms and a bunch of local restaurants that you can visit.DJs are not allowed. Loud music and parties are strictly prohibited. It's a very quiet, relaxing, and peaceful neighborhood. No smoking inside the house.check in 3pm check out 11am extra charge. If you don't check out 11am.a minimum of 5 cars, no more than 5 cars

Stunning Hamptons Waterfront Escape w/ Sunset View

Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views and sunset from our spacious deck. Vaulted ceilings and large windows flood the space with natural light. Brand new Weber Grill (2025). We have completed renovations of 3 bathrooms, 2 kitchens, and the entire pool house over the last 18 months. Our home is <10 minutes drive to the beach, groceries, and restaurants! Our pool will open May 23, 2026 and close on Labor Day.

Coastal Retreat|Heated Saltwater Pool|5 MinToBeach

Unwind in Hamptons Bliss! A coastal oasis awaits at this exquisite vacation house. Immerse yourself in luxury, from the elegant interiors to the serene outdoor retreat including a massive fenced-in salt water heated pool (Memorial Day to Labor Day) that will leave you in awe. Indulge in beachside bliss, upscale shopping, and culinary delights. Create memories that will linger long after the sun sets over the horizon. Your dream Hamptons getaway starts here!

Hampton's Haven

5 bedroom, 3.5 bath contemporary ranch style home, with custom shaped heated pool and meticulously maintained 7 seater hot tub. Expansive patio w/outdoor dining for 10 - close to beach, town and more! Our home has comfortable office space with gigabit wifi throughout! Fabulous game room with ping pong, 4 person air hockey, smart tv and board game lounge. Everything you'll need for a memorable gathering of friends or the perfect family vacation!

3Bed/2 Bath - Hamptons Getaway w/ Heated Pool!

Newly renovated and professionally decorated Hamptons home. Located in Hampton Bays just a 5 min drive to beaches, waterfront restaurants, wineries & golf courses. Open floor plan single family home w/ 3 bedrooms, 2 full baths, spacious living room with games and dining room. Large outdoor heated pool. Pool heat is an additional cost. Comfortably fits a group of 6.